Sodium Carbonate → 4,5-Dichloro-4-fluoro-3,4,5,6-tetrahydrophthalic anhydride

HRID 1109827Notes

Reaction equation

HRID 1109827 reaction equation
[Cl:1][C:2]1[CH2:3][C:4]2[C:9](=[O:10])[O:8][C:6](=[O:7])[C:5]=2[CH2:11][CH:12]=1.[Cl:13]N1C(=O)CCC1=O.C1C=CN=CC=1.[FH:27].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1([F:27])[CH:12]([Cl:13])[CH2:11][C:5]2[C:6]([O:8][C:9](=[O:10])[C:4]=2[CH2:3]1)=[O:7]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 31398ChlorosuccinimideHCID 64774Pyridine, hydrofluoride (1:1)HCID 109869774-Chloro-3,6-dihydrophthalic anhydride

Product 1

HCID 542227594,5-Dichloro-4-fluoro-3,4,5,6-tetrahydrophthalic anhydride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-chloro-3,6-dihydrophthalic anhydride (0.63 g) and N-chlorosuccinimide (0.47 g) in methylene chloride (6.2 ml) was added to pyridinium poly(hydrogen fluoride) at room temperature. The reaction mixture was stirred for 2 hours and then carefully poured into a two phase system containing solid sodium carbonate and methylene chloride. The suspension was filtered, the methylene chloride layer was dried over magnesium sulfate and the solvent removed under reduced pressure.

Workup

  1. additioncarefully poured into a two phase system
  2. filtrationThe suspension was filtered
  3. dry with materialthe methylene chloride layer was dried over magnesium sulfate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4dd89edc0a244d408f3a9325994de888
Source dataset
uspto-grants-1994_06
Patent number
US05322954

Reaction notes

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